flights to Chicago
Finding cheap flights to Chicago is easy when you have all the right information and tips to secure the cheapest airfares. Whether it is a business trip, a family visit, or an event, Chicago offers one of the most well-connected and competitive air markets in the world. This means visitors can easily find multiple affordable airfare options if they know where to look and book smart.
At Farehoper, we help you find the best airline prices, affordable routes, and schedules in one place so you can book the right flight at the best price.
Why Chicago Is a Top Flight Destination
Chicago is a major hub for domestic and international travel. It is the third-largest city in the United States, popular for its business, culture, sports, food and entertainment.
Travelers fly to Chicago for:
- Corporate meetings and conventions.
- Family vacations and weekend getaways.
- Sports events and concerts.
- Universities and academic travel.
- Tourism and sightseeing.
With two major airports and dozens of airlines competing for passengers, Chicago is often one of the cheapest major U.S. cities to fly into.
Chicago Airports – Where Will You Land?
Chicago has two main airports, each serving different types of travelers.
O’Hare International Airport (ORD)
O’Hare is one of the busiest airports in the world and the primary international gateway to Chicago.
Key facts about O’Hare International Airport (ORD):
- Located about 17 miles northwest of downtown
- Major hub for United Airlines and American Airlines
- Serves domestic and international routes
- Excellent public transportation via the CTA Blue Line
Best for:
International travelers, long-haul routes, and those wanting the widest airline choice.
Midway International Airport (MDW)
Midway is smaller and closer to downtown.
Key facts about Midway International Airport (MDW):
- About 10 miles from downtown
- Major base for Southwest Airlines
- Focuses on domestic and short-haul routes
- Often cheaper for U.S. flights
Best for:
Budget travelers, short trips, and domestic flights.
How to Find Cheap Flights to Chicago
Securing affordable airfare is all about timing, flexibility and smart comparison. If you want to be a pro in finding the budget flights, follow the tips below:-
Book in advance – Tracking prices for your route as early as possible is the best way to book cheap flights to Chicago. It is best to book 3-6 weeks in advance for domestic flights and 2-4 months in advance for international flights to secure the best flight deal.
Be Flexible With Dates – Being flexible with travel dates can save you a lot, even by a day. The cheapest days to fly are Tuesday, Wednesday, and Thursday. Avoid weekends, as they see high travel leading to costly tickets.
Travel in the Off-Season – January, February, and early March are the cheapest months to fly to Chicago. It is the best month for people looking to travel on a budget. Airlines are lowering airfares due to lower travel demand compared to the peak travel season.
Avoid peak travel season – June, July, August, and the holiday season starting in December is the high travel season, where airfares become expensive. High travel demand and completion lead to steep ticket rates.
Compare Airfares – Use multiple travel booking platforms to compare fares across airlines and find the cheapest flights to Chicago.
What Impacts the Price of Flights to Chicago?
Multiple factors affect the price of flights to Chicago. Airfares Demand (holidays, events, conventions)
- Departure city
- Time of booking
- Baggage rules
- Seat availability
Best Time to Visit Chicago (Weather + Prices)
Spring (April–June) – Mild weather with fewer crowds. It is the perfect time for outdoor activities and visiting popular tourist attractions. Flight prices are moderate during the season.
Summer (July–September) – It is the peak tourist season featuring festivals and outdoor events. The weather is warm and lively, ideal for beach adventure, but the airfares are costly.
Fall (October–November) – Temperatures begin to decrease, offering beautiful outdoor autumn scenery. The season offers a perfect balance of airfare and comfort.
Winter (December–March): Chicago experiences cold, snowy conditions and icy roads. It also offers the cheapest flight and hotel rates, perfect for budget travelers. However, ticket prices may rise in the second half of December due to the holiday season.
Airlines Serve Chicago
Major airlines serving Chicago include:
- United Airlines (hub)
- American Airlines (hub)
- Delta Air Lines
- Southwest Airlines (MDW base)
- JetBlue
- Alaska Airlines
- Spirit Airlines
- Frontier Airlines
Getting from the Airport to Downtown Chicago From O’Hare (ORD)
CTA Blue Line – 45 min to downtown
- Taxi / Uber / Lyft – 30–60 min
- Shuttle services available
From Midway (MDW)
- CTA Orange Line – 25 min to downtown
- Rideshare & taxis
Top Attractions in Chicago
Millennium Park & Cloud Gate (“The Bean”) – Millennium Park is one of the most popular places to visit in Chicago. Located in downtown, major attraction includes Cloud Gate, also known as “The Bean”, a colossal mirror sculpture that reflects the city skyline. It is a perfect place to visit, take photos, explore other attractions like the Jay Pritzker Pavilion and the Crown Fountain, and enjoy seasonal events such as ice skating and concerts.
Navy Pier – Navy Pier is an ideal family spot in Chicago. It stretches into Lake Michigan and offers entertainment and attractions for all ages. However, the star attraction is the famous Centennial Wheel, which offers panoramic city views.
Willis Tower Skydeck – Willis Tower is one of the tallest buildings in the Western Hemisphere. Formerly known as the Sears Tower, the Skydeck on the 103rd floor features The Ledge, a glass box that protrudes, offering thrilling views of the city.
Art Institute of Chicago – The Art Institute of Chicago is an iconic museum and one of the oldest in the world. It houses masterpiece works like American Gothic and Nighthawks. It is a must-visit for art lovers.
The Magnificent Mile – It is a premium shopping destination featuring luxury stores, restaurants, boutiques, and historic buildings. For those not interested in shopping, the place offers a perfect spot to walk, eat, and people-watch.
Lakefront Beaches – Chicago is home to popular beaches like North Avenue Beach, Oak Street Beach, and 12th Street Beach, ideal for swimming, biking and enjoying the cool vibe and scenic lake views.
Frequently Asked Questions – Cheap Flights to Chicago
Is Chicago cheap to fly to?
Yes, Chicago is cheap to fly because it is a huge airline hub with multiple airlines competing on prices.
What is the cheapest airport to fly into in Chicago?
If you are flying domestically from a U.S. city, Midway Airport (MDW) offers cheaper flights. For international routes, O’Hare (ORD) offers multiple options and better connectivity.
What is the cheapest month to fly to Chicago?
January and February are typically the cheapest months due to low demand and cold weather.
What is the cheapest day of the week to fly to Chicago?
Tuesday and Wednesday are generally the cheapest days to fly to Chicago.
How far in advance should I book flights to Chicago?
For domestic flights, it is usually best to book 3-6 weeks ahead. And for international trips, 2-4 months is a must if looking for cheap flights to Chicago.
Are last-minute flights to Chicago expensive?
It depends, but especially waiting for a cheap last-minute flight is risky. However, domestic last-minute deals are possible, especially if you are flexible with travel date, time and airports.
Do budget airlines fly to Chicago?
Southwest, Spirit, and Frontier offer low-cost flights to Chicago, especially into Midway (MDW).
Is O’Hare (ORD) or Midway (MDW) better for downtown access?
Both are convenient. ORD has the Blue Line train, and MDW has the Orange Line—both connect directly to downtown.
Can I save money by flying with only a carry-on?
Yes. Many cheap fares don’t include checked baggage. Packing light can save you $30–$70 per bag.